Hydrochloric Acid → Hydrochloric Acid

Participants

Reaction Steps

The product from Example 59 (2.9211 g, 6.053 mmol) and anisole (2 drops) were mixed in AcOH (10 mL) and 4N HCl (10 mL) and stirred at 25° C. overnight, fitted with a drying tube. The mixture was adjusted to pH 13 with 1N NaOH with stirring in ice-H2O and then extracted with CH2Cl2 (2×70 mL). The combined organic fraction was dried (Na2SO4), filtered through celite, and evaporated. The product was gravity column chromatographed eluting with CHCl3:2% NH3 before it was converted to the HCl salt with Et2O—HCl to yield 15 HCl.(0.5531 g, 22%, unoptimized): m.p. (HCl salt) 200° C. (dec); 1H NMR (HCl salt, DMSO-d6) δ1.98 (br s, 4H, —CH2CH2—), 2.86 (s, 3H, —NCH3), 3.2-4.3 (complex, 8H, 4 —CH2—), 7.16 (d, J=7.4 Hz, 2H, aromatic), 7.33 (d, J=7.5 Hz, 2H, aromatic), 7.7 (m, 2H, aromatic), 8.08 (s, 1H, aromatic), 8.23 (m, 1H, aromatic). MS(FAB) m/z 383. Anal. (C, H, N) C21H26N4O30.2HCl.0.75H2O.

Provenance & Evidence